Senior Commercial Underwriting Manager - Jacksonville, FL

Senior Commercial Underwriting Manager

Jacksonville, Florida | On‑Site

Join our collaborative team where you will have meaningful opportunities for growth and advancement. Our small, nimble structure means your experience will be rewarded with autonomy and the ability to impact results. Enjoy a positive, friendly work environment with accessible leadership.

Stillwater Insurance Group is an admitted, AM Best and Demotech rated, mid‑sized P & C insurance company offering a variety of home, auto and commercial insurance products in a 50 state US market. We are headquartered in Jacksonville, Florida, with additional offices in New York and Omaha, Nebraska. Our employees consistently describe Stillwater as a great company with great people where honesty and integrity are high priorities.

As a Stillwater team member you will make a difference every day, help grow the company and interact with emerging technologies. Coaching and development, recognition, and professional growth are some of the benefits of working in our small team environment.

We are seeking a Senior Commercial Underwriting Manager to lead commercial underwriting operations, portfolio performance, and underwriting team development. This role is responsible for driving profitable growth through disciplined underwriting practices, effective risk management, operational excellence, and strong agency relationships.

The Senior Commercial Underwriting Manager will oversee underwriting staff, guide complex risk decisions, monitor portfolio results, and partner with executive leadership to execute strategic growth initiatives while maintaining underwriting profitability.

This position offers the opportunity to play a key leadership role within a growing organization where decisions are made quickly and contributions are highly visible. The ideal candidate is both strategic and hands‑on, capable of balancing team leadership with execution and operational oversight.

Unlike larger organizations with multiple layers of management, this role provides direct interaction with senior leadership and the ability to make a meaningful impact across the business.

• Lead day-to-day management of underwriting commercial programs and operational initiatives.
• Oversee workflow execution, process improvement efforts, and service delivery standards.
• Monitor program performance metrics and identify opportunities for operational enhancement.
• Support implementation of new initiatives, products, and business strategies.
• Ensure projects and deliverables are completed efficiently and aligned with organizational goals.

• Oversee the end-to-end evaluation of targeted new and renewal commercial business, ensuring compliance with established risk appetites.
• Collaborate with actuarial, claims, and product teams to design, launch, and refine commercial coverage forms and product offerings.
• Identify areas of concern regarding loss ratios and risk trends, applying strategic remediation.

• Develop, implement, and monitor pricing models, tools, and methodologies to ensure competitive yet profitable rates across all segments.
• Review terms, and conditions for high‑value and complex accounts.
• Monitor competitive landscape and legislative/regulatory changes to adjust pricing strategies and product guidelines proactively.

• Manage and mentor small commercial underwriting operations and product management team.
• Foster a collaborative, accountable, and high‑performing work environment.
• Provide coaching, performance feedback, and professional development support.
• Help establish priorities, allocate resources, and improve team effectiveness.

• Partner with leadership, claims, operations, compliance, analytics, and distribution teams to support business objectives.
• Coordinate across departments to improve communication, execution, and customer experience.
• Assist with vendor, agency, and partner relationships as needed.
• Support strategic initiatives and operational planning efforts.

• Identify…